I haven't debugged and check it completely so it may contain some errors,
But the general idea is to get all three sorting parameters out of the string in the collection:
First letter - String sort.
Number - Numberic sort.
Last letter - String sort.
and then create an object that contains all three and sort accordingly.
var items = new List<string> { "S1", "S10", "S10A", "S10B", "S10C", "S1A", "S1B", "S1C", "S1D" };
var result = items.
Select(o =>
{
var firstLetter = o[0];
int lastLetterNumber;
var lastChar = o[o.Length - 1].ToString();
var lastLetterForSort = Int32.TryParse(lastChar, out lastLetterNumber) ? string.Empty : lastChar;
var number = o.Substring(1, lastLetterForSort.Equals(string.Empty) ? o.Length - 1 : o.Length - 2);
return new {
FirstLetter = firstLetter ,
Number = Int32.Parse( number) ,
LastLetter = lastLetterForSort ,
Value = o
};
}).
OrderBy(o => o.FirstLetter).
ThenBy(o => o.Number).
ThenBy(o => o.LastLetter).
Select(o => o.Value).
ToList();
hope it helps.